Demonic Times
by MaddieMakeshift
Summary: Annie Keurig is a seventeen year old demon. When she teams up with Sam, Dean, and Castiel, some shocking facts are uncovered. Rated R for violence, swearing, and sexual content
1. Welcome to Hell

I hear a yelp and smile to myself. The hell hounds are always so faithful.

"Sam!" Dean yells.

"Aggredior!" Nate yells at the hounds.

I step into the moonlight. "Mitigandae, claudicates!" The hounds immediately back off the Winchesters. I squat down next to them, stroking their necks. "Good boys." I glance up at the brothers. "Make sure you hold onto them tightly, but don't kill them. I've waited so long for this moment."

"What are you going to do with us?" Castiel asks. "And who are you?"

I smile at him. "Ah, Castiel. I almost forgot about you. You and I, we've met before. When Gabriel trapped Sam and Dean in TV-land, we became…acquainted."

"You!" Castiel says angrily.

"My name is Annie Keurig. And, honestly, you have to trust that I'll help you survive in today's world. These are my friends, Nate, Jason, Miles, and Tom. We can offer you protection."

"You're a demon!" Dean says.

"And what's so bad about that?" I ask innocently. "Let's be honest, you aren't in any position to bargain."

"What's in it for you?" Sam asks.

"That is our business." Miles says.

"It's our lives!" Sam snaps. Nate takes a menacing step forward, but I lay a restraining hand on his shoulder.

"He has a point." I say. I face the trio. "Crowley's plan is to open the Gates of Hell and free the demons and Lucifer from his cage. But you see, my friends and I happen to like humans. And if Lucifer comes back, he will exterminate them. If we have you three on our side, we'll be able to fight against Crowley's corruptness. If you're with us, we protect you from other demons. Got it?"

"We've trusted demons before, and it hasn't helped at all. How do we know we can trust you?" Castiel asks.

"You don't." Nate begins.

"But you have to." Jason finishes. I shake my head at their moment of twin telepathy.

"We're your best bet at taking down Crowley." Tom adds.

"So what'll it be, boys?" I ask. They share a few uncertain glances with each other.

Finally, Castiel lets out a sigh. "They're our best choice. Besides, they have us cornered."

I smile widely. "I knew you'd come along. I think we're going to have fun together."

"How did you and Gabriel team up?" Dean asks as we walk back to the house my friends and I are staying in.

"Much like how we did… Common enemies. Which, speaking of enemies, leads me to a question of my own. Why did you give up so easily back there?"

"Because I'm tired of fighting." Dean says after a moment. "I don't want to worry about Lucifer or Crowley or Demons anymore."

"You and me both." I say. "It's tiring." I point at a small house ahead of us. "That's where we're staying. 193 North Maple Street."

"Alright." Dean says.

We walk inside, and I glance at the trio. "Your rooms are at the back of the house."

"Thanks." Sam mutters, and shoulders past me. Dean walks past me and rests his hand on my shoulder for a second before moving away.

"Wait!" I say to Dean. He turns around. "Please don't try to leave tonight while we're asleep. You're… You're our last hope. We _need_ you."

Dean looks down at me with an expression I don't understand. It's almost as if he wants to feel sorry for me, but is not allowing himself to. "Yeah, yeah." Then he turns and walks away with Castiel.

I face Nate. "Do you think they'll stay?"

"There's no telling. Should we get Caleo to do a protective spell?" He asks.

I think of my friend, the witch. "No, we shouldn't. We need to learn how to trust them." Nate pulls me into him and kisses me on the lips. I wrap my arms around his neck. "I really hope this will work."


	2. Explanations

I stretch out, feeling my tense muscles. I open my eyes to see Nate's peaceful face next to mine. I poke his cheek with my index finger in a repetitive fashion. He bats my finger away and lets out a sigh.

"We should get up now." I say.

"Let's not." Nate says.

"We have to. We should talk with the Winchesters." I say, getting up and crossing the room to pull on some clothes. I settle for leggings and a white cotton long sleeved shirt.

I skip out into the kitchen, full of hope. I freeze when I see a girl with porcelain skin and long blonde hair setting down a plate of waffles in front of Dean. Nate runs into me. "What the hell, Annie?" He asks, and then looks up and sees the girl. "Oh, shit." He mutters.

"Caleo. What're you doing here? I thought you were in MysticFalls, dealing with Niklaus Mikaelson." I say, my voice audibly shaking. I see Sam turn to stare at me while Dean ignores everything except for his waffles.

"Well, I guess you thought wrong." Caleo says tightly, walking over to me. "Now, tell me, what are _you_ doing with the Winchesters?"

My jaw tightens. "I was planning on telling you, Caleo, just not now. I know how busy you are with that vampire-werewolf hybrid." I shrug.

"What are you talking about?" Sam asks. Caleo and I hold our eye contact and ignore him.

Finally, Caleo sighs. "You could've just told me over the phone."

I smirk. "You would've wanted to come up here and see for yourself." She laughs.

"You're right." Caleo approaches me. "I know how long you've waited for this opportunity." I nod. "Why don't we all plan out what you're going to do. In case you don't remember, your spur-of-the-moment ideas never work."

I run a finger down the scar on my left arm. It goes from the crook of my elbow to my wrist. I flinch. "Yeah, I remember."

"Just be careful." Caleo says, signifying the end of our conversation. She crosses the room the rest of the way to give me a long hug. "I missed have your insane ass around."

"And I missed have your emotional one around." I shoot back with a smirk. She pulls away and laughs.

"I'll be on my way back to MysticFalls later today. I just had to check up on you." Caleo says.

"Consider me checked." I tease, and walk over to the kitchen counter to get myself some waffles. I settle down next to Sam and begin to eat.

The day passes slowly, and most of it is spent separate from the Winchesters. They stay with Castiel in the kitchen, discussing if teaming up with us is really the best option. I hear the words "Kevin", "gates", and "God" several times.

I stay with my friends and Caleo. Eventually, she stands and stretches. "I think it's time that I go back. I'm sure Audra's nearly going insane without me there in MysticFalls."

"Audra? Who's that?" I ask.

"This nymph I've befriended over the years. You two should meet sometime." Caleo says.

I nod. "Maybe after everything to do with demons is taken care of." I say as I give her a hug.

She pokes her head in the kitchen. "Bye, everyone. It was really nice to meet you all. I hope that you decide to trust Annie. She's trying to do the right thing." She gives us one last wave, and leaves.

Dean, Sam, and Castiel walk into the room. "We've made our decision." Sam says, glancing at me shyly.

"Oh?" Is all I can say.

"We'll join you." Dean says, almost reluctantly.

Before I can speak, Castiel begins talking. "But be assured that we don't trust you." I nod slowly.

"Not yet." I say, and tuck my feet under me. "We should talk strategy."

"Agreed." Castiel says, and stands to the left of me as Dean and Sam sit on the couch. Nate and Jason wrinkle their noses at the same time and slide off of the couch to the floor. I roll my eyes at them while Sam and Dean exchange an uncomfortable look.

"Be nice, they're on our side." I chastise the twins. They avoid my eyes. "Anyways, the easiest way to get rid of Crowley is to get him at his most vulnerable. I've known Crowley for a few years. In this town, he owns one bar and one club. The bar I've been working in is called Demonic Times. I've been working there to gain his trust. It's working. I have a shift in about one hour. Caleo's given me a book of spells that you'll need to get in undetected. Crowley will expect me and the boys, but not you three."

"But this is just phase one." Jason interrupts. "Phase two will be accomplished in two days, after Annie turns eighteen." I see Sam give me a surprised glance. "Crowley's club is sort of like a burlesque club and is the equivalent of a Hooter's, called Sin."

"Now you're talking!" Dean says with a smile. I scoff, but smile internally when I see Miles giving Dean an appreciative nod.

"Crowley's been salivating over Annie ever since she showed up a couple years back. As soon as she's legal, he's promoting her to work at Sin. It's a pretty seedy place, but that's where he lets his guard down the most. We'll strike there." Jason continues.

"The only demon Crowley ever liked more than Annie was that bartender, Casey." Miles tacks on.

"Hey!" I snap. "That's a sore topic." Dean snickers.

"It's about time for your shift. You should go and get ready." Tom says to me. I nod and stand.

I turn on the shower in the bedroom I share with Nate and wash myself as quickly as possible. A few minutes later, I unpin my hair and let it fall down my back. I pull on my clothes and strap on all of the required jewelry and accessories. I finish my make up in record time.

I grab my black heels and my diamond mask and head into the living room. "Hey, Nate, could you tie the mask for me?"

Nate plucks the mask from my hands, moves behind me, and ties it around my head. He leans close to me and presses his lips to my ear. "You look beautiful." I can't keep a goofy grin from spreading on my face.

"Can you two save the dirty talk for later?" Jason wrinkles his nose, causing a blush to spread over my cheeks.

"Don't be angry with me, just because I'm getting some and you aren't." Nate laughs. Jason reaches out to tackle him, and I leap out of the way. Miles and Tom pile on top of them.

"Do you ever get tired of being the only girl around them?" Sam asks.

I shake my head. "Nope, not really. I mean, they're practically my family. I love them all." I turn to the boys. "Guys! Come on, stop fucking around."

"Yes, ma'am." Tom salutes and stands. "Are you going to do the spell, or should I?" Tom asks.

"I will. You always mess up concealment spells." I turn to the Winchesters and Castiel. "I'm going to perform a spell. To everyone in this room, you will look like yourselves. But to anyone else, you'll look unfamiliar. The people in Demonic Times will think you're demons. So no funny business and no angel stuff, okay?" I say. They nod. "Then let me get started."

I light some candles and close my eyes, calling a concealment sigil to mind. I pick up a Sharpie from the table and gesture to Sam. "What?"

"Sit down and lift up your shirt. I'm going to have to draw this on your chest." I say. Dean chokes out a laugh as Sam lifts his shirt slowly. "Don't be shy." I smirk and duck down. I draw the sigil on his chest, going over the lines a few times. "Dean, your turn." I draw the sigil on Dean's chest, and then on Castiel's suit jacket. The black is invisible on the black cloth.

"Let's go." Nate says happily, grabbing my hand and tugging me towards the door.

"Wait. I need to warn them, first." I say, looking back at the Winchesters. "You're going to see a lot of unethical things in this bar. There will be demons, vampires, and other supernatural creatures. I need you to promise me that you won't go after them. They'll be hurting people. They'll ask all of us if we'd like a human at the door. Don't feel like you have to say yes. I will say yes, because it's expected of me. Like I said, don't go after them, it will blow our cover. The only way to stop these monsters from hurting more people is to get Crowley. Are we clear?"

The trio nods slowly, disgust clearly written on their faces. "Think of it as a necessary evil." Nate advises as he opens the door. We make the short journey to the bar, and I open the door.

"Annie!" My partner bartender, Matt, calls out. "I saved you a good one!" He says with a laugh, shoving a man older than me in my direction. His hand is around his neck, blood leaking out from under his palm. His eyes show his pure terror.

I set one hand on his chest and give him a warm smile. "What's your name?"

He looks at me, practically shaking. "Evan."

"That's a nice name. Why don't you let me take a look at your injury?" I ask, my voice like velvet. He slowly lifts his hand away from the obvious vampire bite mark. His blood continues to flow down his muscled neck.

"Will you help me?" He asks in a quiet voice. My smile grows, and I shove him roughly against the wall behind him, my mouth attaching to his bleeding wound. I suck the blood from his body as I vaguely hear his screams. I try to stop myself from puking. I hate blood, I hate hurting people, and I hate it when humans scream in pain.

I feel Evan's protests grow weaker, and his body begins to collapse. I don't stop until I hear Crowley's familiar voice from behind me. "Annie, love, that's enough." I step away from Evan and allow him to collapse. "No need to kill the man."

I turn to Crowley with a playful smirk on my face. "But that's always the best part!" I wipe my mouth with the back of my hand.

"You brought friends, I see. New recruits?"

"Of course. Before you ask, they won't take a human. Still too ripe. You know how I was when I started." I grab my black apron and hold it up to my waist and turn my back to Crowley. "Tie me up?"

Crowley takes the strings and ties the apron tightly around my waist, allowing his hands to rest on my hips. "I think it's tied, Crowley." Nate says, his voice tight. I hold in a laugh and glance at Nate over my shoulder, sending him a slight smile.

"Crowley's obsession with you is getting a little bit creepy." Matt says, leaning over to whisper in my ear. "Are you okay to hold down the fort for a few minutes? I need a break."

"Yeah, go ahead and take a break." I say. Matt walks off towards the bathroom. I turn back to the counter and see that my group has found seats right in front of me.

"How're you feeling?" Nate asks. He understands how hard everything to do with Crowley is for me.

"Alright. I almost threw up. I hate human blood." A shudder runs through me.

"Necessary evil." Miles reminds me.

"It'll all be over soon." Tom chimes in.

"But for now, a scotch will be fine." Jason tacks on. I shoot him a mock glare, but fill up a glass with scotch and hand it to him. He tosses it back and smiles at me. "Would you be angry if I forced your boyfriend to go dance with another demon?"

"Not at all." I smile back.

Nate, Jason, Miles, and Tom head out onto the dance floor, leaving me alone with the Winchesters and Castiel.

"So killing people actually makes you sick?" Dean asks.

I plant a beer bottle in front of him and Sam. "Yes. But not because I find it hard to end a human's life. I mean, with reason, it's no issue. But killing like this…just for pleasure…doesn't feel right. I can't help but feel that Gabriel would be disappointed with me." I say.

"Were you and Gabriel close?" Sam asks.

"Yes. He was like my brother, in more ways than one." I say. Castiel looks at me with an odd expression on his face.

"When he was killed by…" Sam begins.

I interrupt quickly. "Please, don't start talking about his death. I know the son of a bitch who killed him, I know how he died, and I know where. I don't want to relive that night, okay?" Sam nods.

"I'm just surprised that you two knew each other." Dean says, taking a swig out of his bottle.

"There's a lot of things you don't know about me, Dean." I respond with a smile.

After that short conversation, my shift goes by considerably quickly. Before I know it, it's time to head home. "C'mon, can't we stay for a little bit longer?" Miles begs, eyeing a pretty vampire with dark black hair.

I roll my eyes. "She'll be here tomorrow, she's a regular." Miles sighs. He opens his mouth to respond, but is cut off by a bright light outside and a screeching noise.

Most of the supernatural creatures in the bar are able to escape through the back door, but all demons scream, unable to leave. We begin dropping like flies.

My head pounds, and I feel a warm liquid leak from my eyes. Just as sudden as the light came, it vanishes. I touch my wet cheek. My hand comes away red with blood. I sit on the floor, stunned.

"Are you alright?" Sam asks, tilting my face up towards his. "You're crying blood!"

"What the hell was that?" Dean asks.

"I have no clue." I say, my eyes meeting Crowley's. Tear tracks of blood mark his cheeks as well.

"You should go home, Annie. Protect your house with every sigil you know, just to be safe. I'll see you at Sin in two days." Crowley spins on his heel and leaves through the back door.

Sam helps me to my feet. "Castiel, do you know what happened? Maybe it was something in heaven?" Tom asks.

"My connection to heaven has been severed. It might have been an angel. We need to get back to the house." Castiel says.

We race back to the house, checking over our shoulders the entire way there. I am terrified of what might be out there. I walk in the door first.

"Everyone, grab markers. We're going to need to mark every door, window, and vent in this place." I say, turning my head to talk to them. Sam and Dean's eyes widen at something behind me. I turn and see Adam Milligan, Michael's vessel.

Michael smiles at me. "What the hell do we do?" I hear Tom hiss behind me.

"Shut the door." I say, my eyes never leaving Michael's face. "How did you get out of the cage?"

"Oh, Annie. It's good to see you, too." Michael says. Nate, Jason, Miles, and Tom immediately recoil away from me. "You haven't told them?"

"Michael, don't." I warn, my eyes turning black. "You've caused enough people to leave me."

"You chose your side, sister. To the angels, this is merely compensation for your actions." Michael turns to my friends.

"Sister?" Castiel asks. I refuse to make eye contact with any of them. His eyes grow wide when I nod at him slowly, knowing that he understands what is happening.

Michael continues speaking. "Would you like to tell them, or should I?"

"I will." I say, taking a deep breath. "I lied. My name isn't Annie; it's Angel. I'm not a real demon. I'm an archangel, a daughter of God, and Michael is my brother."


End file.
